


Drag Queens Have More Fun

by LIKEABOSS1234



Category: Supernatural
Genre: Castiel is Jack Kline's Parent, Dean Winchester is Jack Kline's Parent, Dean is a Sassy Bitch, Drag Queens, M/M
Language: English
Status: Completed
Published: 2018-12-22
Updated: 2018-12-22
Packaged: 2019-09-24 22:47:20
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,744
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17109608
Author URL: https://archiveofourown.org/users/LIKEABOSS1234/pseuds/LIKEABOSS1234





	Drag Queens Have More Fun

Alexandria is an oc. Also Jack is 4 in this.

••••••••••••••••

   "Hello?" Sam answers the phone. "Hey, Sam. It's Alexandria. I'm having a bit of a ... problem at my bar and I need you and Dean to come help," Alexandria giggles a bit. "Okay, what do you need," Sam asks. "Come tonight and I'll show you," Alexandria says and hangs up quickly.  

 

   "Dean!" Sam yells. "What?! You're gonna wake Jack if you're not careful. Cas just got him to sleep," Dean says. "We have to go help out Alexandria at her bar tonight. She said she had a problem and that'll show us what it is tonight," Sam explains. "Okay, let's get ready," Dean says.

 

   "Sam, Dean, I'm relieved you've come so quickly. I need a drag queen and a waiter for the rest of the week. So who's doing which?" Alexandria says quickly, adjust her tight dress. "Dean will be the drag queen since he has a more feminine frame. I'll be the waiter," Sam says, quickly. "Okie dokie, come on, Dean," Alexandria takes hold of Dean's shoulders as he shouts curse words and protests at her and Sam.   

 

   Alexandria takes a measuring tape and goes around Dean's waist then goes to find a corset 5 inches smaller. It was a waist and down only corset, as Alexandria was planning on filling out the chest which would be hard with a full corset. "Ok so you're gonna need to take off your shirt, sweetie. Just tell me when you have the corset on and then I'll come tie it tight," Dean does as instructed. "Ok, I guess I'm ready," Dean says. "Ok, this is going to feel very weird," Alexandria warns as she pulls the corset very tight around Dean's midsection, slimming out the rest of his stomach as well as making his waist very small. "Okay so next up is padding and filling out the chest area. So I have got a Double D cup bra that we are going to make look like you have cleavage," Alexandria helps him put the bra on and then helps put the breast enhancement pads inside as well as stuffing it with tissue paper. She then contours them to make them look real. "Ok so for padding, I have this," She shows Dean a very thick padding," It's for people who have a little bit less of a curvy body. It will make your hips and butt look huge in comparison to your tiny, little waist."   

 

   They get the padding on and Dean is starting to very much look like a woman with more exaggerated features. "Can I pick out what dress I want?" Dean asks, unsure of himself. "Of course, sweetie. There is a whole closet full over there," Alexandria says.

 

 

   Dean picks a two piece crop top and skirt with a slit from just about where his hip is down to the bottom. "Oh my god, girl. You are going to slay in that," Alexandria says," And I knew which wig I wanted to use on you before we started so let me get it."  

 

 

   

   "Okay, sweetie just sit in that chair and I'll make sure the wig is secure and then we can start on makeup," Alexandria smiles as she puts the wig over Dean's short hair. She makes sure it won't fall off then starts on makeup.  

 

 

 

   She finishes the main makeup and then softens up Dean's features. She gives him long eyelashes, high cheekbones and huge lips that are honestly unreal. "Kay, baby girl. You're done with the look for the most part," She says, giddily, and leans down to kiss his cheek,"Let me go get the last thing."

 

  

   "Wait, what?" Dean says, confused,"I won't be able to walk in those."  

 

  "Don't worry Deanna. I'll teach you how as well as I'll teach you how to be more feminine when you go up to males to get money," Alexandria smiles,"Which honestly we've definitely got our work cut out for us gal."   

 

   "So Deanna, put on the heels and try to walk," Dean does this and struts beautifully, swinging his exaggerated hips and working his facial expressions. "OH MY GOODNESS! You're doing great baby girl," Deanna giggles...Wait! Dean giggles. "Okay so when going to men, you must be very feminine and very submissive so show me you're best girly voice," Alexandria says. "Ok, how's this," Dean does a female's voice like it's the most natural thing in the world. "OH MY G! HOW ARE YOU SO GOOD," She exclaims, excitedly,"You are absolutely perfect for the rest of the week."  

 

   Dean had forgotten he'd be here all week and is suddenly very smiley and giddy. Unlike Dean, at any time. "Okay baby girl, you are so amazing," Alexandria says,"Let's go get your brother since he will be in drag as well." "Huh," Dean says, puzzled,"I thought only one of us would be in drag."      "Yeah, I forgot to mention both of you would've been in drag, but one would be  performing, which is you, and he'll be a waitress. Are you okay with that, Deanna?" Dean nods, surprisingly being okay with being called a girl version of his own name and being in drag. He felt happy, at home. "I'm very okay with that," Dean giggles like a little girl. "Awww. You are an adorable girly girl. We should do this more often after this week," Alexandria says, booping Deanna's nose. "Totally," Deanna slips into like a girl persona. "You beautiful , beautiful girl," Alexandria bends down to kiss Deanna's cheek once more and then they walk to get Sam.   

 

   Sam looks at his brother and almost doesn't recognize him. He looks like a beautiful woman. His waist was cinched, his padding gave him a huge ass and hips, he had actually breasts. He looked like a woman Sam would date, but this was his brother.     

 

   "May I introduce you to, Deanna," Alexandria says and Dean struts forward, does a sexy dance and sassily shakes his stuff as he walks away. "Heya Sammy," Gosh he even sounded like a girl. "You're turn, Samantha. Come on, sweetie," Alexandria grabbed his hand in hers and they walked back to the dressing room, him protesting the whole time. "I thought only one of us was gonna be in drag," Sam says. "This is a drag bar, and you thought you would just be a waiter. Nope, you're going to be a beautiful waitress," Alexandria smiles.  

 

   "Okay, baby. So I'm gonna give you a figure just like I gave Deanna. Just take off your shirt and slip the corset on the table on," Sam does this. "Okay so you have a little more to work with for the breasts, Samantha. So I have a triple D bra. Put it on and we'll get it looking like you have breasts right after I tighten the corset," Alexandria pulls the strings on the corset and Sam lets out a moan. Alexandria ignores this and ties the corset as tight as she can. "Alexandria? Why did you want us to do this?" Sam asks. "Because you guys are beautiful as men, I wanted to make you beautiful as women," Alexandria says as she helps Sam out on his padding. "Ok so next, your outfit. It's right over here. Let me go get it."(This is what the outfit consisted of)   

 

 

 

Sam stares at her as if she grown another head. "Sorry about how bad it is. You're new though so the outfits will get better with the week," Alexandria explains. "Why the daddy's girl choker," Sam asks. "You need to look submissive, but also kinky. And if men see you with that they'll fall over themselves," She explains,"Now get dressed so I can do your makeup and wig."   

 

   Sam quickly gets dresses in his costume finding the heels surprisingly easy to walk in. He clasps the choker then walks over to Alexandria's chair. "Okay, sweet girl. Let's put this wig on you," She says. She grabs a huge blonde wig that was styled in a huge beehive updo.

 

 

 

 

   "Oh my goodness. You look so pretty let's just soften those manly features," she covers all the hair on his face and then puts foundation on and goes through her planned look. It's a dark eye look with natural looking arched eyebrows, a beauty mark and deep red lips.

   "Are you kidding? Both you and your brother look gorgeous as women," Alexandria exclaims. Sam looked in the mirror. He looked hot, like smoking hot. "Men out there are gonna love you, Samantha," She continues. Sam has a much harder time catching on to the female thing, but eventually he got it. "Let's get you out there sweetheart," Alexandria says and pushes him onto the floor to be a waitress.

 

  "Deanna, baby girl. Are you ready," Deanna bounces up in his ten inch heels, giggling and acting like a little girl who had gotten into their mother's makeup. "Yep, yep, yep," Dean says, in his girly voice. "Good job, baby. You're next up," The drag queen before Deanna walks off the stage.

 

   "Next to the stage, we have Deanna," Deanna struts onto the stage, the spotlight hits her and goes for it. She did the splits, went in the crowd and twerked on men and teased them by sitting on their lap and being all flirty. She went back to the stage, did more sexy moves and then struts backstage again. "Oh my Gosh. You totally did slay queen. Damn," Alexandria says.

 

   Dean went to the dressing room to see Cas had texted him a picture of him hold Jack with a book resting on his other leg.

 

   He sends back a mirror selfie and says 'Blame Sammy.'

Cas: you look great.

Dean: Good cause I've got to do this for the rest of the week.

 

   It gets to be closing time and Sam walks back into the dressing room. He had an interesting evening of having to be a basically stripper to the men in the audience. He had gotten several ass smacks, involuntary kisses and money shoved in to his clothes. But other than that, he didn't really mind being in drag.  

 

  "We should get back in our other clothes and get home," Dean says, wanting to get home to his husband and baby boy. They took off all their makeup and clothes and got in their own clothes and then drove back home.


End file.
